(E)-ethyl 4-(4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxyphenoxy)butanoate | 1436428-56-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (E)-ethyl 4-(4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxyphenoxy)butanoate
• 英文别名: ethyl 4-[4-[(E)-2-(1,3-diethyl-7-methyl-2,6-dioxopurin-8-yl)ethenyl]-2-methoxyphenoxy]butanoate
• CAS: 1436428-56-6
• 化学式: C₂₅H₃₂N₄O₆
• 分子量: 484.552
• InChiKey: KTZQUJCYNZBBFO-WYMLVPIESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  35
• 可旋转键数：
  12
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  103
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (E)-ethyl 4-(4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxyphenoxy)butanoate 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以88%的产率得到(E)-4-(4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxyphenoxy)butanoic acid
  参考文献：
  名称：

  Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space

  摘要：

  Growing evidence has suggested a role in targeting the adenosine A(2A) receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A(2A) receptor were synthesized and tested in a recombinant human adenosine A(2A) receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A(2A) receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A(2A) receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.070
• 作为产物：
  描述：

  (E)-4-(3-((6-amino-1,3-diethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)amino)-3-oxoprop-1-en-1-yl)-2-methoxyphenyl acetate 在 硫酸氢铵 、 lithium aluminium tetrahydride 、 六甲基二硅烷 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 150.0 ℃ 、900.02 kPa 条件下， 反应 75.0h， 生成 (E)-ethyl 4-(4-(2-(1,3-diethyl-7-methyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-yl)vinyl)-2-methoxyphenoxy)butanoate
  参考文献：
  名称：

  Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space

  摘要：

  Growing evidence has suggested a role in targeting the adenosine A(2A) receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A(2A) receptor were synthesized and tested in a recombinant human adenosine A(2A) receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A(2A) receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A(2A) receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2013.03.070

文献信息

• Novel adenosine A2A receptor ligands: A synthetic, functional and computational investigation of selected literature adenosine A2A receptor antagonists for extending into extracellular space
  作者：Manuela Jörg、Jeremy Shonberg、Frankie S. Mak、Neil D. Miller、Elizabeth Yuriev、Peter J. Scammells、Ben Capuano

  DOI：10.1016/j.bmcl.2013.03.070

  日期：2013.6

  Growing evidence has suggested a role in targeting the adenosine A(2A) receptor for the treatment of Parkinson's disease. The literature compounds KW 6002 (2) and ZM 241385 (5) were used as a starting point from which a series of novel ligands targeting the adenosine A(2A) receptor were synthesized and tested in a recombinant human adenosine A(2A) receptor functional assay. In order to further explore these molecules, we investigated the biological effects of assorted linkers attached to different positions on selected adenosine A(2A) receptor antagonists, and assessed their potential binding modes using molecular docking studies. The results suggest that linking from the phenolic oxygen of selected adenosine A(2A) receptor antagonists is relatively well tolerated due to the extension towards extracellular space, and leads to the potential of attaching further functionality from this position. Crown Copyright (C) 2013 Published by Elsevier Ltd. All rights reserved.